Sodium Carbonate → HCID 67973310、化合物

HRID 1184696ノート

反応式

HRID 1184696 の反応式
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19](B4OC(C)(C)C(C)(C)O4)[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].Br[C:32]1[CH:37]=[CH:36][C:35]([S:38][CH3:39])=[CH:34][C:33]=1[CH3:40].C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH:1]([O:4][C:5]([N:7]1[CH2:8][CH2:9][CH:10]([CH:13]2[CH2:17][C:16]3[CH:18]=[C:19]([C:32]4[CH:37]=[CH:36][C:35]([S:38][CH3:39])=[CH:34][C:33]=4[CH3:40])[CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:11][CH2:12]1)=[O:6])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 26370189(4-Bromo-3-methylphenyl)(methyl)sulfaneHCID 67973765HCID 67973765、化合物

生成物 1

HCID 67973310HCID 67973310、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a mixture of 4-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-benzofuran-2-yl]-piperidine-1-carboxylic acid isopropyl ester (150 mg), 1-bromo-2-methyl-4-methylsulfanyl-benzene (60 mg), in N,N-dimethylformamide (3 mL) a 2 M aqueous Na2CO3 solution (0.29 mL) is added. The mixture is sparged with argon for 10 min and PdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (19 mg) is added. The resulting mixture is stirred for 6 h at 90° C. After cooling to room temperature, water and methanol are added and the aqueous phase is extracted with ethyl acetate. The organic phase is concentrated and the residue is purified by HPLC on reversed phase (MeOH/H2O/TFA). Yield: 56 mg (56% of theory); LC (method 2): tR=1.70 min; Mass spectrum (ESI+): m/z=426 [M+H]+.

後処理

  1. customThe mixture is sparged with argon for 10 min
  2. additionPdCl2[1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (19 mg) is added
  3. temperatureAfter cooling to room temperature
  4. additionwater and methanol are added
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. concentrationThe organic phase is concentrated
  7. customthe residue is purified by HPLC on reversed phase (MeOH/H2O/TFA)

出典と根拠

ORDレコード
ord-2b250d6587684415a512c5dc60611b13
出典データセット
uspto-grants-2014_03
特許番号
US08669271B2

反応ノート

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