Acetic Acid → 2-((3-(7-Bromo-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-methoxybenzoic acid

HRID 2361368Notes

Reaction equation

HRID 2361368 reaction equation
[NH2:1][C:2]1[C:3]([CH3:25])=[C:4]([C:8]2[C:20]3[C:19]4[C:14](=[CH:15][C:16]([Br:21])=[CH:17][CH:18]=4)[NH:13][C:12]=3[C:11]([C:22]([NH2:24])=[O:23])=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH:26]([C:28]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:29]=1[C:30]([OH:32])=[O:31])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl.O1CCCC1>[Br:21][C:16]1[CH:15]=[C:14]2[C:19]([C:20]3[C:8]([C:4]4[C:3]([CH3:25])=[C:2]([NH:1][CH2:26][C:28]5[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:29]=5[C:30]([OH:32])=[O:31])[CH:7]=[CH:6][CH:5]=4)=[CH:9][N:10]=[C:11]([C:22](=[O:23])[NH2:24])[C:12]=3[NH:13]2)=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 71762052-Formyl-5-methoxybenzoic acidHCID 679947214-(3-amino-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxamide

Product 1

HCID 679947572-((3-(7-Bromo-1-carbamoyl-9H-pyrido[3,4-b]indol-4-yl)-2-methylphenylamino)methyl)-5-methoxybenzoic acidYield 163.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(3-amino-2-methylphenyl)-7-bromo-9H-pyrido[3,4-b]indole-1-carboxamide (0.184 g, 0.466 mmol), 2-formyl-5-methoxybenzoic acid (0.210 g, 1.164 mmol), sodium triacetoxyborohydride (0.296 g, 1.397 mmol), and acetic acid (0.067 mL, 1.164 mmol) in dichloromethane (14 mL) and tetrahydrofuran (14 mL) was stirred at room temperature for 16 hr. The reaction was quenched with water (30 mL) and the mixture was extracted with ethyl acetate (3×40 mL). The combined extract was washed with brine (30 ml) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the crude desired product (0.425 g, 0.760 mmol, 163% yield) as a beige solid. The crude product was used in the next step without further purification.

Workup

  1. customThe reaction was quenched with water (30 mL)
  2. extractionthe mixture was extracted with ethyl acetate (3×40 mL)
  3. extractionThe combined extract
  4. washwas washed with brine (30 ml)
  5. dry with materialdried over anhydrous MgSO4
  6. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-e90dc2631de545a880baed1c836e1449
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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