Sodium Carbonate → 4-(2-fluoropyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1042259

反応式

HRID 1042259 の反応式
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:11][C:12]1[C:17](B(O)O)=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[F:11][C:12]1[C:17]([C:2]2[C:3]3[CH:10]=[CH:9][NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:16][CH:15]=[CH:14][N:13]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27832702-Fluoropyridine-3-boronic acidHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

生成物 1

HCID 596273704-(2-fluoropyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine収率 17%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (7.68 g, 50 mmol), 2-fluoropyridin-3-ylboronic acid (10.57 g, 75 mmol), and tetrakis(triphenylphosphine)palladium(0) (2.89 g, 2.5 mmol) was suspended in DME (300 mL) and aqueous sodium carbonate (10%) (50 mL, 100 mmol). The suspension was heated at reflux over night, cooled to r.t. and the reaction mixture was partitioned between EtOAc (300 mL) and NaHCO3 (aq., sat., 200 mL). The aqueous layer was washed with EtOAc twice. The organic layers were combined and washed with brine, then loaded on silica and purified via flash column (EtOAc:hexane=50-95%) on ISCO to give 4-(2-fluoropyridin-3-yl)-7H-pyrrolo[2,3-d]pyrimidine as a light yellow solid with a green tint (1.85 g, 17% yield). MS (ESI, pos. ion) m/z: 214 [M+H]+

後処理

  1. temperatureThe suspension was heated
  2. temperatureat reflux over night
  3. customthe reaction mixture was partitioned between EtOAc (300 mL) and NaHCO3 (aq., sat., 200 mL)
  4. washThe aqueous layer was washed with EtOAc twice
  5. washwashed with brine
  6. custompurified via flash column (EtOAc:hexane=50-95%) on ISCO

出典と根拠

ORDレコード
ord-f56f02f51a004aaa8565503a101a2944
出典データセット
uspto-grants-2013_10
特許番号
US08557830B2

関連ノート

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