Potassium Hydroxide → (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(2-chloro-3-fluoro-6-methoxyphenyl)methanol

HRID 2095619Notes

Reaction equation

HRID 2095619 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([O:11][CH3:12])[C:3]=1[CH:4]=[O:5].[Br:13][C:14]1[CH:15]=[C:16]2[C:20](=[N:21][CH:22]=1)[NH:19][CH:18]=[CH:17]2.[OH-].[K+]>CO>[Br:13][C:14]1[CH:15]=[C:16]2[C:17]([CH:4]([C:3]3[C:6]([O:11][CH3:12])=[CH:7][CH:8]=[C:9]([F:10])[C:2]=3[Cl:1])[OH:5])=[CH:18][NH:19][C:20]2=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridineHCID 534075982-Chloro-3-fluoro-6-methoxybenzaldehyde

Product 1

HCID 67004061(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)(2-chloro-3-fluoro-6-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-chloro-3-fluoro-6-methoxybenzaldehyde (10.55 g, 55.82 mmol), 5-bromo-7-azaindole (10.0 g, 50.76 mmol) and KOH (4.0 g, 71 mmol) in methanol (200 mL) was stirred at ambient temperature for 12 h. The reaction mixture was quenched with water and the crystallizing solid was filtered and dried to give the title compound as a white solid. 1H NMR (DMSO-d6, 300 MHz): □ δ=3.71 (s, 3H), 5.69 (d, 1H, J=6.3 Hz), 6.55 (d, 1H, J=4.5 Hz), 7.07 (dd, 1H, J=4.5, 4.2 Hz), 7.19 (s, 1H), 7.32 (t, J=8.0 Hz), 8.30 (s, 1H), 9.60 (s, 1H), 11.38 (s, br, 1H).

Workup

  1. customThe reaction mixture was quenched with water
  2. filtrationthe crystallizing solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-c5bbfbb0b3f447f9887becefa6739169
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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