Acetic Acid → HCID 70968055, compound

HRID 239909Notes

Reaction equation

HRID 239909 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:25]=[CH:24][C:9]([C:10]([NH:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17]([CH:22]=O)=[CH:16]4)=[O:11])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[C:26](O)(=O)[CH3:27].[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:44](=[O:47])([O-])O.[Na+].[CH3:49][N:50](C=O)C>O1CCCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:25]=[CH:24][C:9]([C:10]([NH:12][C:13]3[CH:14]=[C:15]4[C:19](=[CH:20][CH:21]=3)[NH:18][C:17]([CH2:22][NH:50][CH2:49][C:26]3([CH3:27])[CH2:44][O:47][CH2:30]3)=[CH:16]4)=[O:11])=[CH:8][CH:7]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86675795HCID 86675795, compound

Product 1

HCID 70968055HCID 70968055, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Cyclopropylmethoxy)-N-(2-formyl-1H-indol-5-yl)benzamide (50 mg) obtained in Reference Example 2,1-(3-methyloxetan-3-yl)methanamine (30 mg) and acetic acid (200 μL) were dissolved in tetrahydrofuran (4 mL)-DMF (1 mL), and the mixture was stirred for 30 min. Sodium triacetoxyborohydride (165 mg) was added and the mixture was stirred at room temperature overnight. To the reaction mixture was added aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate, and washed with saturated brine. The obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [eluent; ethyl acetate:methanol=100:0 (volume ratio)→ethyl acetate:methanol=80:20 (volume ratio)] to give the title compound (40 mg, yield 64%) as a pale-yellow solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography [eluent; ethyl acetate:methanol=100:0 (volume ratio)→ethyl acetate:methanol=80:20 (volume ratio)]

Sources & evidence

ORD record
ord-ebb939ecb2ff443498fdfe088ebe019a
Source dataset
uspto-grants-2014_02
Patent number
US08642770B2

Reaction notes

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