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

HRID 471841ノート

反応式

HRID 471841 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-286c183a88c548e186c62b9dd4c1c966
出典データセット
uspto-grants-2014_01
特許番号
US08633175B2

反応ノート

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