Acetic Acid → N-(3,4-Difluorobenzyl)-2-((dimethylamino)methyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

HRID 40102Notes

Reaction equation

HRID 40102 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[N:11]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:10]=1[CH:27]=O)=[O:8].[CH3:33][NH:34][CH3:35].CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)CCl.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][C:31]=1[F:32])[CH2:5][NH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[N:11]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:10]=1[CH2:27][N:34]([CH3:35])[CH3:33])=[O:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59762371N-(3,4-Difluorobenzyl)-2-formyl-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide2×

Product 1

HCID 69228136N-(3,4-Difluorobenzyl)-2-((dimethylamino)methyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

General Procedure P. To a solution of N-(3,4-difluorobenzyl)-2-formyl-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxamide (Compound 94, 70 mg, 0.16 mmol) in ClCH2CH2Cl (10 ml) at room temperature was added dimethylamine (2 M in THF, 0.24 ml, 0.48 mmol), HOAc (14 μl, 0.24 mmol), and NaBH(OAc)3 (102 mg, 0.48 mmol). The reaction was stirred at room temperature for 16 h, diluted with EtOAc, washed with aqueous Na2CO3 and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (EtOAc, then 9:1 EtOAc-Et3N, then 7:2:1 CH2Cl2-MeOH-Et3N) to yield the title compound as an off-white solid.

Workup

  1. washwashed with aqueous Na2CO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography on silica gel (EtOAc

Sources & evidence

ORD record
ord-36bb6c92b3834e5784e37ffb8561482f
Source dataset
uspto-grants-2013_09
Patent number
US08524917B2

Reaction notes

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