Potassium Carbonate → [2,3'-Bipyridin]-6-amine

HRID 227919

反応式

HRID 227919 の反応式
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+].O>[N:7]1[C:6]([NH2:8])=[CH:5][CH:4]=[CH:3][C:2]=1[C:11]1[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 2062462-Amino-6-chloropyridineHCID 27343783-Pyridinylboronic acid

生成物 1

HCID 11586359[2,3'-Bipyridin]-6-amine収率 85%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate触媒HCID 962Water溶媒

実験手順

The general procedure described in Example 3 was used with 6-chloro-pyridin-2-ylamine (129 mg, 1.00 mmol), 3-pyridylboronic acid (184 mg, 1.50 mmol), Pd(OAc)2 (2.2 mg, 0.010 mmol, 1 mol %), sodium 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl-3′-sulfonate (10.0 mg, 0.020 mmol, 2 mol %), K2CO3 (414 mg, 3.00 mmol), water (2.0 mL), 12 h, 100° C. The product was purified by column chromatography on silica gel (eluting with ethyl acetate/methanol, 9.5/0.5) to give the desired product as a white solid (145 mg, 85%). Mp=108° C. 1H NMR (400 MHz, d4-MeOH) δ: 8.69 (d, 1H, J=4.8 Hz), 8.43 (dd, 1H, J=4.8 Hz, 1.6 Hz), 8.19 (d, 1H, J=4.8 Hz), 7.96 (dq, 1H, J=8.0 Hz, 1.6 Hz, 0.4 Hz), 7.75 (dd, 1H, J=8.8 Hz, 2.4 Hz), 7.44 (qd, 1H, J=4.8 Hz, 8.8 Hz), 6.68 (d, 1H, J=8.4 Hz). 13C NMR (125 MHz, d4-MeOH) δ: 161.0, 148.2, 147.4, 146.5, 137.9, 136.0, 135.4, 125.6, 123.4, 110.6. IR (neat, cm−1): 3396 (br), 2522, 1633, 1018. EI-MS: Theoretical [M+H]=172.0869. Found: 172.0868. Anal. Calcd for C10H9N3: C, 70.16; H, 5.30. Found: C, 69.89; H, 5.25.

後処理

  1. customThe product was purified by column chromatography on silica gel (eluting with ethyl acetate/methanol, 9.5/0.5)

出典と根拠

ORDレコード
ord-187a002042984255b0dcc53906c13063
出典データセット
uspto-grants-2009_07
特許番号
US07560596B2

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