Sodium Carbonate → HCID 86715468, 화합물

HRID 2284565

반응식

HRID 2284565 반응식
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]3[CH:16]=[N:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Br[C:18]1[CH:19]=[C:20]2[N:26](C(OC(C)(C)C)=O)[N:25]=[CH:24][C:21]2=[N:22][CH:23]=1.[Cl:34][C:35]1[C:40](B2OC(C)(C)C(C)(C)O2)=[CH:39][CH:38]=[CH:37][N:36]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]3[CH:16]=[N:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:34][C:35]1[C:40]([C:18]2[CH:19]=[C:20]3[NH:26][N:25]=[CH:24][C:21]3=[N:22][CH:23]=2)=[CH:39][CH:38]=[CH:37][N:36]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 120670602-Chloropyridine-3-boronic acid pinacol esterHCID 86715468HCID 86715468, 화합물HCID 86715472HCID 86715472, 화합물

생성물 2

HCID 86715468HCID 86715468, 화합물HCID 86715473HCID 86715473, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

6-(2-Chloropyridin-3-yl)-1H-pyrazolo[4,3-b]pyridine was synthesized in the similar manner to the preparation of 5-(2-chloropyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine by heating the mixture of tert-butyl 6-bromo-1H-pyrazolo[4,3-b]pyridine-1-carboxylate (2.5 g, 8.4 mmol), 2-chloro-3-pyridine boronic acid pinacol ester (2.2 g, 9.2 mmol), Pd(PPh3)4 (610 mg, 0.52 mmol) and 2M aq.Na2CO3 (12 mL, 24 mmol) in 1,4-dioxane (40 mL). Upon work-up of the reaction mixture similar to 5-(2-chloropyridin-3-yl)-1H-pyrazolo[3,4-b]pyridine provided 6-(2-chloropyridin-3-yl)-1H-pyrazolo[4,3-b]pyridine as an off-white crystalline solid. 1H NMR (DMSO-d6): δ 13.50 (s, 1H), 8.57 (app s, 1H), 8.48 (dd, 1H, J=1.7 and 4.7 Hz), 8.35 (s, 1H), 8.12 (s, 1H), 8.02 (dd, 1H, J=1.7 and 7.6 Hz), 7.60 (dd, 1H, J=4.7 and 7.7 Hz).LCMS: rt 4.50 min (A), purity 94%, MS (m/e) 231 (MH+).

후처리

  1. temperatureby heating

출처 및 근거

ORD 기록
ord-d8ee282988d3428685f6c1cb0dd6b29d
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145433B2

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