Hydrochloric Acid → 2-(2,4-Difluorophenyl)-6-(1-hydroxy-1-methylethyl)isonicotinic acid

HRID 1909125ノート

反応式

HRID 1909125 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([C:19]([CH3:21])=[CH2:20])[N:18]=1)[C:12]([O:14]C)=[O:13].[BH4-].C([N+](CC)(CC)CC)C.[OH-:32].[Na+].Cl>CO.COCCOC>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([C:19]([OH:32])([CH3:21])[CH3:20])[N:18]=1)[C:12]([OH:14])=[O:13]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 28251Tetraethylammonium tetrahydroborate2 回HCID 67339607Methyl 2-(2,4-difluorophenyl)-6-isopropenylisonicotinate

生成物 1

HCID 673396622-(2,4-Difluorophenyl)-6-(1-hydroxy-1-methylethyl)isonicotinic acid収率 74.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To a solution of methyl 2-(2,4-difluorophenyl)-6-isopropenylisonicotinate (0.29 g, 1.01 mmol) in methanol (5.1 mL) and DME (5.1 mL) was added cobalt(II)mesotetraphenylporphine (6.8 mg, 10.1 mmol). The mixture was stirred at ambient temperature. After 18 h, tetraethylammonium borohydride (73.5 mg, 0.51 mmol) was added. After 15 min, additional tetraethylammonium borohydride (0.14 g, 1.01 mmol) was added. After 1.5 h, sodium hydroxide (1.0 M in water; 2.03 mL, 2.03 mmol) was added. The mixture was heated to 50° C. After 1 h, HCl (0.17 mL, 2.03 mmol) was added and the mixture was concentrated. Purification by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (0.22 g). MS 294.1 (M+1).

後処理

  1. waitAfter 15 min
  2. waitAfter 1.5 h
  3. temperatureThe mixture was heated to 50° C
  4. waitAfter 1 h
  5. concentrationthe mixture was concentrated
  6. customPurification by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-a420fb67075e4d03a90704c842265576
出典データセット
uspto-grants-2013_12
特許番号
US08598209B2

反応ノート

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