Sodium Carbonate → HCID 67972151、化合物

HRID 331401ノート

反応式

HRID 331401 の反応式
Br[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([F:11])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH:21]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:29]([O:28][C:26]([N:23]1[CH2:22][CH:21]=[C:20]([C:2]2[C:7]3[CH:8]=[CH:9][O:10][C:6]=3[C:5]([F:11])=[CH:4][CH:3]=2)[CH2:25][CH2:24]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 668005644-Bromo-7-fluoro-1-benzofuran

生成物 1

HCID 67972151HCID 67972151、化合物収率 91.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

A mixture of commercially available 4-bromo-7-fluoro-benzofurane [CAS-No 1194376-46-9] (0.72 g, 3.35 mmol) and commercially available tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.09 g, 3.52 mmol) in 1,2-dimethoxyethane (22 ml) and 2M sodium carbonate solution (5.58 ml, 11.2 mmol) was purged with argon in an ultrasonic bath during 5 min. Then triphenylphosphine (176 mg, 0.67 mmol) and palladium(II)acetate (75.2 mg, 0.34 mmol) were added and the reaction mixture was allowed to stir at 85° C. for 5 h. The reaction mixture was cooled to room temperature, poured into water (50 ml) and extracted with diethyl ether (2×120 ml). The combined organic layers were washed with brine (50 ml), dried (MgSO4) and evaporated. The crude product (1.7 g) was further purified by flash chromatography on silica gel (heptane/ethyl acetate, 0-50%) to yield 4-(7-fluoro-benzofuran-4-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a yellow oil (0.97 g, 91%), MS (ISP) m/z=262.1 [(M+H)+].

後処理

  1. customwas purged with argon in an ultrasonic bath during 5 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionextracted with diethyl ether (2×120 ml)
  4. washThe combined organic layers were washed with brine (50 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product (1.7 g) was further purified by flash chromatography on silica gel (heptane/ethyl acetate, 0-50%)

出典と根拠

ORDレコード
ord-f644b112c4b54ef6ac4e722e294209ee
出典データセット
uspto-grants-2014_11
特許番号
US08877778B2

反応ノート

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