Potassium Phosphate, Tribasic → HCID 59548528、化合物

HRID 1879682ノート

反応式

HRID 1879682 の反応式
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

参加物

9

反応物 4

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

生成物 1

HCID 59548528HCID 59548528、化合物収率 76%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 312751,4-Dioxane溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-b1f7acfe5cdb447b9735ff1f37aeb066
出典データセット
uspto-grants-2012_11
特許番号
US08318719B2

反応ノート

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