Potassium Carbonate → Thiazolo[4,5-c]pyridine-6-carboxylic acid,2-[(1-methylethyl)amino]-,methyl ester

HRID 1452967ノート

反応式

HRID 1452967 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]2[N:8]=[C:9]([NH:11][CH:12]([CH3:14])[CH3:13])[S:10][C:4]=2[CH:3]=1.[C:15]1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:44]([O-:47])([O-])=[O:45].[K+].[K+]>CO.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:12]([NH:11][C:9]1[S:10][C:4]2[CH:3]=[C:2]([C:44]([O:47][CH3:15])=[O:45])[N:7]=[CH:6][C:5]=2[N:8]=1)([CH3:14])[CH3:13]

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 575272276-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine

生成物 1

HCID 57527243Thiazolo[4,5-c]pyridine-6-carboxylic acid,2-[(1-methylethyl)amino]-,methyl ester収率 301.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 6-chloro-N-isopropylthiazolo[4,5-c]pyridin-2-amine (0.24 g, 1.05 mmol, 1.0 eq.), Pd(OAc)2 (0.0313 g, 0.139 mmol, 0.1 eq.), 1,3-bis(diphenylphosphino)propane (0.0443 g, 0.107 mmol, 0.1 eq.) and K2CO3 (0.2214 g, 1.60 mmol, 1.5 eq.) in MeOH (2.6 mL) and DMF (1.3 mL) was stirred under an atmosphere of CO inside a bomb (40 psi) at 91° C. overnight. After cooling to room temperature, the reaction mixture was filtered through Celite and rinsed with MeOH. The filtrate was concentrated in vacuo, diluted with EtOAc and water. The layers were separated, and the organic layer was washed with brine and 10% aqueous LiCl, dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with CH2Cl2:MeOH (10:0.3) to give methyl 2-(isopropylamino)thiazolo[4,5-c]pyridine-6-carboxylate as a white solid (0.081 g, 31% yield).

後処理

  1. filtrationthe reaction mixture was filtered through Celite
  2. washrinsed with MeOH
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiondiluted with EtOAc and water
  5. customThe layers were separated
  6. washthe organic layer was washed with brine and 10% aqueous LiCl
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with CH2Cl2:MeOH (10:0.3)

出典と根拠

ORDレコード
ord-b4d6cabc7d6349d6af2901154b2e17e2
出典データセット
uspto-grants-2009_01
特許番号
US07473784B2

反応ノート

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