Triphenylphosphine → Methyl 1-[2-(4-tert-butoxyphenoxy)ethyl]-4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

HRID 513197노트

반응식

HRID 513197 반응식
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[C:15]([O:19][C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26]O)=[CH:22][CH:21]=1)([CH3:18])([CH3:17])[CH3:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[C:15]([O:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][CH2:26][N:10]2[C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=3[CH:8]=[C:9]2[C:11]([O:13][CH3:14])=[O:12])=[CH:28][CH:29]=1)([CH3:17])([CH3:16])[CH3:18]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 26599236methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylateHCID 712301312-(4-Tert-butoxyphenoxy)ethanol

생성물 1

HCID 86720574Methyl 1-[2-(4-tert-butoxyphenoxy)ethyl]-4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate수율 105%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (500 mg, 2.374 mmole), 2-(4-tert-butoxyphenoxy)ethanol (624 mg, 2.97 mmole), and PPh3 (778 mg, 2.97 mmole) were combined in toluene (10 mL) at RT. To this was added DIAD (0.58 mL, 2.98 mmole) slowly at RT. After 3 hr the mixture was concentrated. Flash column chromatography (Biotage-SNAP-50 g SiO2, 0-25% EtOAc/hexanes) gave the title compound (1.0 g, 105%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.18 (d, J=6.0 Hz, 1 H); 7.44 (d, J=1.0 Hz, 1 H); 7.43-7.38 (m, 1 H); 6.85-6.81 (m, 2 H); 6.64-6.60 (m, 2 H); 4.92 (t, J=5.0 Hz, 2 H); 4.31 (t, J=5.0 Hz, 2 H); 3.95 (s, 3H); 1.26 (s, 9 H).

후처리

  1. concentrationAfter 3 hr the mixture was concentrated

출처 및 근거

ORD 기록
ord-5a388207a6814effb0e693245ea5e253
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102673B2

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