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1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → Tert-butyl 3-(4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoate

HRID 1177572
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HRID 1177572 반응식
CC(C)([O-])C.[Na+].I[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][C:16]3[C:21]([N:22]=2)=[CH:20][CH:19]=[C:18]([C:23]2([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:25][CH2:24]2)[N:17]=3)=[CH:10][CH:9]=1.Cl.[NH2:33][CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:26]1([C:23]2([C:18]3[N:17]=[C:16]4[S:15][C:14]([C:11]5[CH:12]=[CH:13][C:8]([NH:33][CH2:34][CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:9][CH:10]=5)=[N:22][C:21]4=[CH:20][CH:19]=3)[CH2:25][CH2:24]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

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HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 23676156Sodium t-butoxideHCID 671116852-(4-Iodophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine

생성물 1

HCID 67111678Tert-butyl 3-(4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoate

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

Sodium tert-butoxide (21 mg, 0.213 mmol) was added to a mixture of 2-(4-iodophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (40.4 mg, 0.089 mmol), tert-butyl 3-aminopropanoate hydrochloride (19 mg, 0.107 mmol), Pd2(dba)3 (2.0 mg, 2.2 μmol), and Xantphos (5.1 mg, 8.9 μmol) in toluene (1.0 mL), and the resulting mixutre was heated under argon at 80° C. for 15 h. The reaction mixture was then cooled to 25° C. and concentrated onto silica gel. Chromatographic purificaiton (silica gel, 0-50% EtOAc/hexanes) furnished tert-butyl 3-(4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)phenylamino)propanoate as a yellow oil. MS (ESI) m/z: Calculated: 471.2; Observed: 472.1 (M++1).

후처리

  1. temperatureThe reaction mixture was then cooled to 25° C.
  2. concentrationconcentrated onto silica gel

출처 및 근거

ORD 기록
ord-52e6a33dc9f74fed85bd4fd23aca82cf
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842685B2

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