Methanol → HCID 57906514, compound

HRID 420522Notes

Reaction equation

HRID 420522 reaction equation
C[O:2][C:3]([C:5]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[CH:9][N:8]2[CH:19]=[CH:20][N:21]=[C:7]2[CH:6]=1)=O.CO.[Li+].[BH4-]>C1COCC1>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:10]1[C:5]([CH2:3][OH:2])=[CH:6][C:7]2[N:8]([CH:19]=[CH:20][N:21]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 57906615HCID 57906615, compound

Product 1

HCID 57906514HCID 57906514, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (394 mg, 1.23 mmol) and MeOH (0.15 mL, 3.68 mmol) in THF (8 mL) was cooled to 0° C. (ice bath) then LiBH4 (2 M solution in THF, 1.8 mL, 3.6 mmol) was added dropwise and the resulting mixture was heated at 50° C. and stirred for 4 h. The reaction mixture was cooled to RT, quenched by the addition of a saturated NH4Cl solution in water, diluted in water and extracted with AcOEt (2×). The combined organic fractions were dried over Na2SO4, filtered and evaporated to dryness. The remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/MeOH 99:1→8.2) to yield the title compound (156 mg, 0.53 mmol, 43%). MS: 293 [M+1]+; HPLC: AtRet=1.20, TLC: RF 0.20 (DCM/MeOH 95:5).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customquenched by the addition of a saturated NH4Cl solution in water
  3. additiondiluted in water
  4. extractionextracted with AcOEt (2×)
  5. dry with materialThe combined organic fractions were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, DCM/MeOH 99:1→8.2)

Sources & evidence

ORD record
ord-0982d37d9d154dabb56dec9da54e8d69
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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