Sodium Carbonate → HCID 58102398、化合物

HRID 1191893ノート

反応式

HRID 1191893 の反応式
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][N:11]([CH:14]2[CH2:16][CH2:15]2)[C:10](=[O:17])[CH:9]=1.[OH:18][C:19]([CH3:53])([CH3:52])[CH2:20][C@@:21]1([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[O:26][C:25](=[O:27])[N:24]([C@H:28]([C:30]2[CH:35]=[CH:34][C:33](B3OC(C)(C)C(C)(C)O3)=[CH:32][C:31]=2[CH3:45])[CH3:29])[CH2:23][CH2:22]1>CN(C)C=O>[CH:14]1([N:11]2[CH:12]=[CH:13][C:8]([C:33]3[CH:34]=[CH:35][C:30]([C@@H:28]([N:24]4[CH2:23][CH2:22][C@:21]([CH2:20][C:19]([OH:18])([CH3:53])[CH3:52])([C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=5)[O:26][C:25]4=[O:27])[CH3:29])=[C:31]([CH3:45])[CH:32]=3)=[CH:9][C:10]2=[O:17])[CH2:16][CH2:15]1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 58102383HCID 58102383、化合物HCID 596356474-Bromo-1-cyclopropylpyridin-2(1H)-one

生成物 1

HCID 58102398HCID 58102398、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

2 M aqueous Na2CO3 solution (0.41 mL) was added to a mixture of 4-bromo-1-cyclopropyl-1H-pyridin-2-one (0.11 g) and (S)-6-(2-hydroxy-2-methyl-propyl)-3-{(S)-1-[2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one (0.20 g) in N,N-dimethylformamide (2 mL). The resulting mixture was sparged with argon for 10 min prior to the addition of [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (33 mg). The mixture was heated to 100° C. and stirred at this temperature overnight. After cooling the mixture to ambient temperature, water was added and the resulting mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine and dried (MgSO4). The solvent was evaporated and the residue was purified by HPLC on reversed phase (methanol/water/NH4OH) to afford the title compound. Yield: 0.13 g (64% of theory); LC-MS (Method 5): tR=3.43 min; Mass spectrum (ESI+): m/z=501 [M+H]+.

後処理

  1. customThe resulting mixture was sparged with argon for 10 min
  2. additionto the addition of [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) dichloromethane complex (33 mg)
  3. temperatureAfter cooling the mixture to ambient temperature
  4. additionwater was added
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customthe residue was purified by HPLC on reversed phase (methanol/water/NH4OH)

出典と根拠

ORDレコード
ord-dddccc0a7c8b42aa8a39fce73b622729
出典データセット
uspto-grants-2014_03
特許番号
US08680093B2

反応ノート

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