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

HRID 513197ノート

反応式

HRID 513197 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  1. concentrationAfter 3 hr the mixture was concentrated

出典と根拠

ORDレコード
ord-5a388207a6814effb0e693245ea5e253
出典データセット
uspto-grants-2015_08
特許番号
US09102673B2

反応ノート

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