Triphenylphosphine → HCID 58896487, compound

HRID 2235568Notes

Reaction equation

HRID 2235568 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][C:10]2[N:14]([CH3:15])[C:13]3[C:16]([N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=[CH:19][C:12]=3[N:11]=2)=[C:6]([OH:8])[CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Br:58][CH2:59][CH2:60][CH2:61]O>O1CCCC1>[Br:58][CH2:59][CH2:60][CH2:61][O:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[NH:9][C:10]1[N:14]([CH3:15])[C:13]2[C:16]([N:20]([CH2:24][CH2:25][CH3:26])[CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=[CH:19][C:12]=2[N:11]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 123083-Bromo-1-propanolHCID 5462977Diethyl azodicarboxylateHCID 58896585HCID 58896585, compound

Product 1

HCID 58896487HCID 58896487, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 100 mg (0.27 mmol) of 5-chloro-2-(7-dipropylamino-1-methyl-1H-benzimidazol-2-ylamino)phenol in 4 mL of tetrahydrofuran was added 77 mg (0.30 mmol) of triphenylphosphine and 51 mg (0.30 mmol) of diethylazodicarboxylate and the reaction mixture was stirred for 90 minutes at room temperature. To the reaction mixture was added 41 mg (0.30 mmol) of 3-bromopropan-1-ol and the reaction was stirred overnight. The reaction was concentrated in vacuo and the resulting residue was purified by flash chromatography eluting with 20% ethyl acetate/hexanes to give 100 mg (76%) of the title compound.

Workup

  1. stirringthe reaction was stirred overnight
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe resulting residue was purified by flash chromatography
  4. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-86e9de1c112a46f3a2a13b76ba83754b
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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