3-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde → HCID 68635762, compound

HRID 1177489Notes

Reaction equation

HRID 1177489 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:21][CH2:20]1)[N:13]=2)[CH:5]=[O:6].[CH2:28]([Mg]Br)[CH3:29]>O1CCCC1.C(OC)(C)(C)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]([OH:6])[CH2:28][CH3:29])[CH:7]=[CH:8][C:9]=1[C:10]1[S:11][C:12]2[C:17]([N:18]=1)=[CH:16][CH:15]=[C:14]([C:19]1([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][CH2:21]1)[N:13]=2

Participants

5

Reactant 2

HCID 591749073-Fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 68635762HCID 68635762, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzaldehyde (1.00 g, 2.7 mmol) in tetrahydrofuran (20 ml) at 0° C. was added ethylmagnesium bromide soln in t-butylmethyl ether. (4.0 ml, 4.0 mmol) dropwise over 5 min. The reaction was allowed to stir 20 min at 0° C. The reaction was quenched with NH4Cl aq. sat soln. The solid was removed by filtration. The filtrate was concentrated and purified by silica gel chromatography: ISCO, 120 g column, 20-30% EtOAc/Hex, followed by 40% (3% EtN3 in EtOAc)/Hex to give 1-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)propan-1-ol. MS (ESI) m/z: Calculated: 404.1; Observed: 405.1 (M++H).

Workup

  1. customThe reaction was quenched with NH4Cl aq.
  2. customThe solid was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-93aac1e99d13452bae17f4130f9ff0f9
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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