Sodium Bicarbonate → [3-(4-Bromo-2-{[2-(4-fluoro-phenyl)-1,1-dimethyl-ethylamino]-methyl}-phenoxy)-phenyl]-acetic acid methyl ester

HRID 1969018Notes

Reaction equation

HRID 1969018 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH:19]=O)[CH:6]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]([NH2:33])([CH3:32])[CH3:31])=[CH:25][CH:24]=1.C([BH3-])#N.[Na+].C([O-])(O)=O.[Na+]>CO.C(O)(=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][NH:33][C:30]([CH3:32])([CH3:31])[CH2:29][C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)[CH:6]=1

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5184711-(4-Fluorophenyl)-2-methyl-2-aminopropaneHCID 5003444Sodium cyanoborohydrideHCID 58237467[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester

Product 1

HCID 58288539[3-(4-Bromo-2-{[2-(4-fluoro-phenyl)-1,1-dimethyl-ethylamino]-methyl}-phenoxy)-phenyl]-acetic acid methyl ester

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

[3-(4-Bromo-2-formyl-phenoxy)-phenyl]-acetic acid methyl ester (0.150 g, 0.43 mmol), 1-(4-fluorophenyl)-2-methyl-2-propylamine (0.079 g, 0.47 mmol), and sodium cyanoborohydride (0.041 g, 0.65 mmol) were combined in MeOH (2 mL). Acetic acid (2 drops) was added, and the reaction was stirred for 5 hours at room temperature. The mixture was worked-up with EtOAc and saturated aqueous NaHCO3, and the organic layer was dried and concentrated to give the title compound.

Workup

  1. customthe organic layer was dried
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ceb90742decf4890a5113f3cb71be915
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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