Triphenylphosphine → HCID 59700023, compound

HRID 729868Notes

Reaction equation

HRID 729868 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[N:34]1([CH2:39][CH2:40][OH:41])[CH2:38][CH2:37][CH2:36][CH2:35]1.[CH3:42][O:43][C:44]1[CH:49]=[C:48]([C:50]2[CH:51]=[C:52]3[C:58]([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=4[O:65][CH3:66])=[CH:57][NH:56][C:53]3=[N:54][CH:55]=2)[CH:47]=[CH:46][C:45]=1O>C(Cl)Cl>[CH3:66][O:65][C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][C:59]=1[C:58]1[C:52]2[C:53](=[N:54][CH:55]=[C:50]([C:48]3[CH:47]=[CH:46][C:45]([O:41][CH2:40][CH2:39][N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[C:44]([O:43][CH3:42])[CH:49]=3)[CH:51]=2)[NH:56][CH:57]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 762881-PyrrolidineethanolHCID 16039068HCID 16039068, compound

Product 1

HCID 59700023HCID 59700023, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an 8 ml borosilicate reaction vial were added 150 mg (0.350 mmol) of PS-triphenylphosphine (2.33 mmol·g−1; Argonaut Technologies) and anhydrous methylene chloride (5 ml). The vial was fitted with a rubber septum and the suspension was stirred for 5 minutes in an ice-bath (0° C.). Diisopropyl azodicarboxylate (68 μL, 0.35 mmol) was added dropwise, and the mixture was allowed to warm to room temperature over 20 minutes. To the reaction vial was added 2-pyrrolidin-1-yl-ethanol (54 mg, 0.47 mmol) and 2-methoxy-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]phenol (60 mg, 0.17 mmol), and the suspension was stirred at room temperature for 8 hours. The yellow reaction mixture was filtered, and the resin was washed three times with DCM and ether, then twice with DCM. The combined filtrate was concentrated to obtain a yellow residue, which was purified by flash chromatography on amine functionalized silica gel (ISCO RediSep® amine column) using a gradient of ethyl acetate in hexanes to afford 12 mg (8%) of 3-(2-methoxy-phenyl)-5-[3-methoxy-4-(2-pyrrolidin-1-yl-ethoxy)-phenyl]-1H-pyrrolo[2,3-b]pyridine as a light yellow powder. 1H-NMR(d6-DMSO) δ=11.87 (br.s, 1H), 8.51 (d, 1H), 8.18 (s, 1H), 8.11 (d, 1H), 7.70 (d, 1H), 7.57 (dd, 1H), 7.27 (m, 1H), 7.24 (d, 1H), 7.17 (dd, 1H), 7.12 (dd, 1H), 7.06 (s, 1H), 7.04 (m, 1H), 4.08 (t, 2H), 3.85 (s, 3H), 3.83 (s, 3H), 2.82 (t, 2H), 2.55 (m, 4H), 1.69 (m, 4H); MS m/z: 444 [MH]+.

Workup

  1. customTo an 8 ml borosilicate reaction
  2. customThe vial was fitted with a rubber septum
  3. temperatureto warm to room temperature over 20 minutes
  4. stirringthe suspension was stirred at room temperature for 8 hours
  5. filtrationThe yellow reaction mixture was filtered
  6. washthe resin was washed three times with DCM and ether
  7. concentrationThe combined filtrate was concentrated
  8. customto obtain a yellow residue, which
  9. customwas purified by flash chromatography on amine functionalized silica gel (ISCO RediSep® amine column)

Sources & evidence

ORD record
ord-879086b4cee84df6aa62031093b1487b
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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