Sodium Carbonate → HCID 59264873、化合物

HRID 1693647ノート

反応式

HRID 1693647 の反応式
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=[CH:10]2)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[Cl:29][C:30]1[CH:35]=[C:34]([O:36][Si](C(C)(C)C)(C)C)[CH:33]=[CH:32][C:31]=1B(O)O>COCCOC.O.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:29][C:30]1[CH:35]=[C:34]([OH:36])[CH:33]=[CH:32][C:31]=1[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=[CH:10]2

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 21107087(4-((tert-Butyldimethylsilyl)oxy)-2-chlorophenyl)boronic acidHCID 22622428Methyl 6-(((trifluoromethyl)sulfonyl)oxy)-1-naphthoate

生成物 1

HCID 59264873HCID 59264873、化合物収率 82%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of methyl 6-{[(trifluoromethyl)sulfonyl]oxy}-1-naphthoate (0.97 g, 2.91 mmol), tetrakis(triphenylphosphine)palladium (0) (0.13 g, 0.116 mmol), 2 M Na2CO3 (13.6 mL) and 2-chloro-4-[((1,1-dimethylethyl)dimethylsilyl)oxy]phenylboronic acid (1 g, 3.49 mmol) in ethylene glycol dimethyl ether (15.5 mL) was heated at 80° C. for 40 minutes. The reaction mixture was cooled to room temperature, diluted with water and EtOAc, and transferred to a separatory funnel. The organic phase was separated, washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated to give the crude product as an oil. The crude material was purified by flash chromatography over SiO2 with a Hex:EtOAc (0 to 20% EtOAc) gradient to afford 0.74 g (82%) of the title compound as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.06 (s, 1 H), 8.75 (d, J=9 Hz, 1 H), 8.22 (d, J=8 Hz, 1 H), 8.13 (d, J=7 Hz, 1 H), 8.01 (s, 1 H), 7.68 (m, 1 H), 7.61 (t, J=8 Hz, 1 H), 7.34 (d, J=9 Hz, 1 H), 6.96 (m, 1H), 6.86 (m, 1 H), 3.93 (s, 3 H).

後処理

  1. customtransferred to a separatory funnel
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto give the crude product as an oil
  8. customThe crude material was purified by flash chromatography over SiO2 with a Hex

出典と根拠

ORDレコード
ord-a114c7b9a8484c43a5022bfab9d84ac9
出典データセット
uspto-grants-2012_04
特許番号
US08158665B2

反応ノート

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