Potassium Phosphate, Tribasic → HCID 59548528, 화합물

HRID 1879682노트

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HRID 1879682 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[NH:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:13]=1.[CH:14]1(B(O)O)[CH2:16][CH2:15]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:14]1([C:2]2[CH:3]=[CH:4][C:5]3[C:11](=[O:12])[NH:10][CH2:9][CH2:8][NH:7][C:6]=3[CH:13]=2)[CH2:16][CH2:15]1

참가 물질

9

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 595485548-Bromo-3,4-dihydro-1H-benzo[e][1,4]diazepin-5(2H)-one

생성물 1

HCID 59548528HCID 59548528, 화합물수율 76%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 8-Bromo-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (1.02 g, 4.23 mmol, 1 eq), cyclopropylboronic acid (480 mg, 5.5 mmol, 1.3 eq), tricyclohexylphosphine (121 mg, 0.42 mmol, 0.1 eq), Pd(OAc)2 (48 mg, 0.211 mmol, 0.05 eq), K3PO4 (3.2 g, 14.8 mmol, 3.5 eq) in Toluene (40 mL), water (4 mL), dioxane (10 mL), was degassed with argon and heated to 110 C for 15 hours. The reaction was cooled, diluted with ethyl acetate, washed sat. aq. Sodium bicarbonate solution, brine, and dried over mgso4, filtered, concentrated in vacuo and purified with flash chromatography on a silica gel column eluting with 50% ethyl acetate in hexanes to give 650 mg 8-Cyclopropyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one, 76%.

후처리

  1. customwas degassed with argon
  2. temperatureheated to 110 C for 15 hours
  3. temperatureThe reaction was cooled
  4. additiondiluted with ethyl acetate
  5. washwashed sat. aq. Sodium bicarbonate solution, brine
  6. customdried over mgso4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified with flash chromatography on a silica gel column
  10. washeluting with 50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-b1f7acfe5cdb447b9735ff1f37aeb066
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318719B2

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