Acetic Acid → {4-[(2,3-dihydro-1H-inden-2-ylamino)methyl]-3,5-difluorophenyl}boronic acid

HRID 471841Notes

Reaction equation

HRID 471841 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH2:10].[F:11][C:12]1[CH:13]=[C:14]([B:21]([OH:23])[OH:22])[CH:15]=[C:16]([F:20])[C:17]=1[CH:18]=O.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][CH2:18][C:17]1[C:16]([F:20])=[CH:15][C:14]([B:21]([OH:23])[OH:22])=[CH:13][C:12]=1[F:11]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 763102-AminoindaneHCID 5049666Sodium triacetoxyborohydrideHCID 162177083,5-Difluoro-4-formylphenylboronic acid

Product 1

HCID 59316459{4-[(2,3-dihydro-1H-inden-2-ylamino)methyl]-3,5-difluorophenyl}boronic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2,3-dihydro-1H-inden-2-amine (0.780 mL, 5.99 mmol), (3,5-difluoro-4-formylphenyl)boronic acid (1.0 g, 5.99 mmol) and acetic acid (0.710 mL, 12.0 mmol) in THF (12 mL) was stirred at room temperature for 1 hr. To the solution was added NaBH(OAc)3 (3.81 g, 18.0 mmol) and the mixture stirred at room temperature for 16 hr. The mixture was diluted with EtOAc then washed with satd Na2CO3. The combined layers were filtered and the filter cake washed with H2O and EtOAc to give {4-[(2,3-dihydro-1H-inden-2-ylamino)methyl]-3,5-difluorophenyl}boronic acid as a beige glass. LC/MS (method A) tR 0.48 min; m/z 304 (M+H).

Workup

  1. stirringthe mixture stirred at room temperature for 16 hr
  2. washthen washed with satd Na2CO3
  3. filtrationThe combined layers were filtered
  4. washthe filter cake washed with H2O and EtOAc

Sources & evidence

ORD record
ord-286c183a88c548e186c62b9dd4c1c966
Source dataset
uspto-grants-2014_01
Patent number
US08633175B2

Reaction notes

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