Ethyl Acetate → 4-(5-Chloro-2-methylbenzoxazol-6-yl)phenylamine

HRID 407105

반응식

HRID 407105 반응식
Br[C:2]1[C:11]([Cl:12])=[CH:10][C:5]2[N:6]=[C:7]([CH3:9])[O:8][C:4]=2[CH:3]=1.Cl.[NH2:14][C:15]1[CH:20]=[C:19](B(O)O)[CH:18]=[CH:17][CH:16]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(=O)OCC>C(#N)C.O1CCOCC1.O.CCCCCC.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[Cl:12][C:11]1[C:2]([C:18]2[CH:19]=[CH:20][C:15]([NH2:14])=[CH:16][CH:17]=2)=[CH:3][C:4]2[O:8][C:7]([CH3:9])=[N:6][C:5]=2[CH:10]=1

참가 물질

10

반응물 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 27632413-Aminophenylboronic acid hydrochlorideHCID 584874386-Bromo-5-chloro-2-methylbenzoxazole

생성물 1

HCID 674672954-(5-Chloro-2-methylbenzoxazol-6-yl)phenylamine수율 42%

시약·촉매·용매 5

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)촉매HCID 962Water용매HCID 6342Acetonitrile용매HCID 8058Hexane용매HCID 312751,4-Dioxane용매

반응 조건

온도
85 °C

실험 절차

A mixture of 6-bromo-5-chloro-2-methylbenzoxazole (54) (160 mg, 0.65 mmol), anilin-5-boronic acid hydrochloride salt (55) (135 mg, 1.2 eq), Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (A-Phos) (46 mg, 0.1 mmol) and K3PO4 (165 mg) in 2 ml ACN, 2 ml dioxane and 0.5 ml H2O was bubbled with argon before heated at 85° C. for 2 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine, dried over Na2SO4, concentrated to dryness. The resulting red solid was dissolved in DCM and subjected to silica gel column purification using 0-60% B (A: hexane; B: 50% EA in hexane) to furnish 70.6 mg 56 as yellow solid (yield: 42%)

후처리

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness
  6. dissolutionThe resulting red solid was dissolved in DCM
  7. customsubjected to silica gel column purification

출처 및 근거

ORD 기록
ord-f85e768951b248fc8c2ae6801d6e5f25
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754219B2

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