2-Methylpropan-2-olate → HCID 67111849, compound

HRID 1177614Notes

Reaction equation

HRID 1177614 reaction equation
[N:1]1[CH2:5][CH:4]=[C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:2]=1.CC(C)([O-])C.Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:25][C:26]3[C:31]([N:32]=2)=[CH:30][CH:29]=[C:28]([C:33]2([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH2:35][CH2:34]2)[N:27]=3)=[C:20]([F:42])[CH:19]=1>C(O)C>[F:42][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[C:24]1[S:25][C:26]2[C:31]([N:32]=1)=[CH:30][CH:29]=[C:28]([C:33]1([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:34][CH2:35]1)[N:27]=2)[CH2:17][N:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N:2]1.[F:42][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[C:24]1[S:25][C:26]2[C:31]([N:32]=1)=[CH:30][CH:29]=[C:28]([C:33]1([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:34][CH2:35]1)[N:27]=2)[CH2:17][N:2]1[C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:5]=[N:1]1

Participants

6

Reactant 3

HCID 45749132-Methylpropan-2-olateHCID 67111838HCID 67111838, compoundHCID 67112058HCID 67112058, compound

Product 2

HCID 67111849HCID 67111849, compoundHCID 67112201HCID 67112201, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

In a sealable tube was dissolved ethyl 5H-pyrazole-3-carboxylate (0.137 g, 0.979 mmol) in ethyl alcohol (3 mL). To the solution was added tert-butoxide (0.0941 g, 0.979 mmol) followed by 2-(4-(bromomethyl)-2-fluorophenyl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine (0.215 g, 0.489 mmol) and the reaction mixture was heated to 70° C. for 1 h. The crude reaction mixture containing an isomeric mixture was concentrated in vacuo and purified by silica gel chromatography to afford ethyl 1-(3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)-1H-pyrazole-3-carboxylate and ethyl 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyl)-1H-pyrazole-5-carboxylate. MS (ESI) m/z: calculated: 498.2; Observed: 499.0 (M++1).

Workup

  1. customThe crude reaction mixture
  2. additioncontaining an isomeric mixture
  3. concentrationwas concentrated in vacuo
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-8258ffc776cb4fcaa12b750eba5c1e87
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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