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

HRID 70307ノート

反応式

HRID 70307 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6d1eb84d3c784a87b4637b0acc33664b
出典データセット
uspto-grants-2014_09
特許番号
US08822518B2

反応ノート

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