Cesium carbonate → 5-morpholino-3-phenyl-7H-thieno[3,2-b]pyran-7-one

HRID 1042023노트

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HRID 1042023 반응식
Br[C:2]1[C:6]2[O:7][C:8]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:9][C:10](=[O:11])[C:5]=2[S:4][CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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.C(COC)OC>[O:15]1[CH2:16][CH2:17][N:12]([C:8]2[O:7][C:6]3[C:2]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:3][S:4][C:5]=3[C:10](=[O:11])[CH:9]=2)[CH2:13][CH2:14]1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 441811783-Bromo-5-(morpholin-4-yl)-7H-thieno[3,2-b]pyran-7-one

생성물 1

HCID 441816005-morpholino-3-phenyl-7H-thieno[3,2-b]pyran-7-one수율 2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

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온도
130 °C

실험 절차

A 2 mL conical microwave vial was charged with a magnetic stirring bar, 3-bromo-5-morpholino-7H-thieno[3,2-b]pyran-7-one (103) (50 mg, 0.16 mmol), phenylboronic acid (29 mg, 0.24 mmol), cesium carbonate (103 mg, 0.32 mmol), tetrakis(triphenylphosphine)palladium(0) (9 mg, 0.008 mmol), and dimethoxyethane (1 mL). The reaction mixture was magnetically stirred and heated via microwave irradiation for 15 minutes at 130° C. Upon cooling to room temperature, the reaction was concentrated in vacuo and purified using high-pressure liquid chromatography to give 5-morpholino-3-phenyl-7H-thieno[3,2-b]pyran-7-one (6) (10 mg, 3.2 μmol) as a white solid.

후처리

  1. additionA 2 mL conical microwave vial was charged with a magnetic stirring bar
  2. temperatureUpon cooling to room temperature
  3. concentrationthe reaction was concentrated in vacuo
  4. custompurified

출처 및 근거

ORD 기록
ord-340fa9f7c2f1493c99be0b2a326949a0
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557807B2

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