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Potassium Phosphate, Tribasic → N-(1-(3-(3,5-difluorophenyl)-benzo[b]thiophen-2-yl)ethyl)-2-methylpropane-2-sulfinamide

HRID 2036601
ノート
印刷プレビュー

反応式

HRID 2036601 の反応式
[F:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([F:8])[CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.Br[C:50]1[C:51]2[CH:67]=[CH:66][CH:65]=[CH:64][C:52]=2[S:53][C:54]=1[CH:55]([NH:57][S:58]([C:60]([CH3:63])([CH3:62])[CH3:61])=[O:59])[CH3:56]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:50]2[C:51]3[CH:67]=[CH:66][CH:65]=[CH:64][C:52]=3[S:53][C:54]=2[CH:55]([NH:57][S:58]([C:60]([CH3:62])([CH3:63])[CH3:61])=[O:59])[CH3:56])[CH:5]=[C:6]([F:8])[CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 58459232N-(1-(3-bromobenzo[b]thiophen-2-yl)ethyl)-2-methylpropane-2-sulfinamide

生成物 1

HCID 58459329N-(1-(3-(3,5-difluorophenyl)-benzo[b]thiophen-2-yl)ethyl)-2-methylpropane-2-sulfinamide

試薬・触媒・溶媒

2
HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

A mixture of 3,5-difluorophenylboronic acid (292 mg, 1.848 mmol), potassium phosphate (0.204 mL, 2.464 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (126 mg, 0.308 mmol), palladium (II) acetate (27.7 mg, 0.123 mmol) and N-(1-(3-bromobenzo[b]thiophen-2-yl)ethyl)-2-methylpropane-2-sulfinamide (444 mg, 1.232 mmol) in Toluene (10 mL) was purged with N2 for 2 min, then heated to 110° C. overnight. After 19 h, the reaction was partitioned between water and EtOAc. The organic layer was stirred over MgSO4, filtered and concentrated under reduced pressure to give amber oil. The product was purified by column chromatography on a silica gel column using 20 to 40% gradient of EtOAc in hexane as eluent to give N-(1-(3-(3,5-difluorophenyl)benzo[b]thiophen-2-yl)ethyl)-2-methylpropane-2-sulfinamide as a colorless glassy solid: 1H NMR (400 MHz, DMSO-d6) δ 1.13 (s, 9H), 1.50 (d, J=6.7 Hz, 3H), 4.64-4.73 (m, 1H), 5.91 (d, J=4.7 Hz, 1H), 7.21 (dd, J=8.4, 2.3 Hz, 2H), 7.34-7.45 (m, 4H), 8.02 (ddd, J=7.5, 1.4, 1.1 Hz, 1H); LC-MS (ESI)] m/z 394.0 [M+H]+.

後処理

  1. customwas purged with N2 for 2 min
  2. customthe reaction was partitioned between water and EtOAc
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give amber oil
  6. customThe product was purified by column chromatography on a silica gel column

出典と根拠

ORDレコード
ord-e8d0327624484013afff11be16dd538f
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08575183B2

反応ノート

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