Potassium Carbonate → tert-butyl 7-(thiazol-5-yl)-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate

HRID 473856노트

반응식

HRID 473856 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:14][C:13]=3[CH:26]=2)O1.Br[C:29]1[S:33][CH:32]=[N:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.O.C(OCC)(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[S:33]1[C:29]([C:9]2[CH:10]=[CH:11][C:12]3[O:18][CH2:17][CH2:16][N:15]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:14][C:13]=3[CH:26]=2)=[CH:30][N:31]=[CH:32]1

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 5460595-BromothiazoleHCID 66820441Tert-butyl 7-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1,4-benzoxazepine-4-carboxylate

생성물 1

HCID 67513975tert-butyl 7-(thiazol-5-yl)-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate수율 70%

시약·촉매·용매 4

HCID 24290Palladium Chloride촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 8857Ethyl Acetate용매HCID 21534740N,N-Dimethylacetamide--water (1/1)용매

실험 절차

A solution of tert-butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate (73 mg, 0.19 mol), 5-bromothiazole (40 mg, 0.26 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (22 mg, 0.03 mmol) and potassium carbonate (0.14 g, 1.0 mmol) in N,N-dimethylacetamide/water 5:1 (5.5 mL) was heated to 90° C. for 1 hour. The cooled reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (30 mL) and brine (20 mL), and then dried over anhydrous sodium sulfate and concentrated. Purified by silica gel column chromatography (ethyl acetate/hexanes, 1:2) to give tert-butyl 7-(thiazol-5-yl)-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate (44 mg, 70% yield). MS (EI) for C17H20N2O3S: 333 (MH+).

후처리

  1. customThe cooled reaction mixture
  2. washwashed with water (30 mL) and brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customPurified by silica gel column chromatography (ethyl acetate/hexanes, 1:2)

출처 및 근거

ORD 기록
ord-663fc8696a014b818c16a72c00f6be7c
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637499B2

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