HCID 58266297, compound → HCID 58266765, compound

HRID 1888594Notes

Reaction equation

HRID 1888594 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:13]=[CH:12][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.I[C:26]1[CH:39]=[N:38][C:29]2[NH:30][C:31]3[CH:36]=[N:35][C:34]([Br:37])=[CH:33][C:32]=3[C:28]=2[CH:27]=1>C(=O)([O-])[O-].[Na+].[Na+].CC1CCCO1.C(Cl)Cl>[Br:37][C:34]1[N:35]=[CH:36][C:31]2[NH:30][C:29]3[N:38]=[CH:39][C:26]([C:14]4[CH:13]=[CH:12][C:4]([CH2:5][N:6]5[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]5)=[C:3]([O:2][CH3:1])[CH:15]=4)=[CH:27][C:28]=3[C:32]=2[CH:33]=1

Participants

6

Reactant 2

HCID 58266297HCID 58266297, compoundHCID 58266444HCID 58266444, compound

Product 1

HCID 58266765HCID 58266765, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 73012-MethyltetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
85 °C

Procedure

A degassed mixture of 1-[2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-piperidine (885 mg, 2.7 mmol), 3-iodo-6-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole (500 mg, 1.3 mmol), 1,1′-[bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (163 mg, 0.2 mmol) in 2N aqueous sodium carbonate solution (10 mL) and 2-methyltetrahydrofuran (20 mL) was heated at 85° C. for 18 h. The cooled reaction mixture was diluted with DCM (100 mL) and washed with water (75 mL). The organic phase was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford a residue (357 mg, 61%) that was used in the next step without purification. 1H NMR (CDCl3, 300 MHz): 8.83 (d, J=2.0 Hz, 1H), 8.70 (s, 1H), 8.63 (d, J=2.0 Hz, 1H), 8.24 (s, 1H), 7.45 (d, J=7.8 Hz, 1H), 7.25 (d, J=7.8 Hz, 1H), 7.14 (s, 1H), 3.96 (s, 3H), 3.65 (s, 2H), 2.56-2.48 (m, 4H), 1.67-1.59 (m, 4H), 1.52-1.41 (m, 2H).

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water (75 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-290a4a9a522f4b959b9a116944bedbcd
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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