Methanol → (3-Nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methanol

HRID 1177518Notes

Reaction equation

HRID 1177518 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[C:14]1[S:15][C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[C:18]([C:23]1([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:25][CH2:24]1)[N:17]=2)[C:7](OC)=[O:8])([O-:3])=[O:2].CO.[BH4-].[Li+]>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=[CH:12][C:13]=1[C:14]1[S:15][C:16]2[C:21]([N:22]=1)=[CH:20][CH:19]=[C:18]([C:23]1([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:24][CH2:25]1)[N:17]=2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 67112770Methyl 3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzoate

Product 1

HCID 67111784(3-Nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of methyl 3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzoate (1.10 g, 2.5 mmol) in THF and methanol (0.31 mL, 7.6 mmol) was added lithium borohydride, 2.0 M solution in tetrahydrofuran (1.9 mL, 3.8 mmol). The reaction mixture was stirred at ambient temp, and upon completion the reaction mixture was cooled to 0° C. was quenched with ice and sat'd aq. NH4Cl carefully. The reaction mixture was partitioned between DCM and sat'd aq. NH4Cl and extracted with DCM. The combined organics were purified by silica gel chromatography, EA/hexanes gradient, to give (3-nitro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methanol as an orage solid. MS (ESI) m/z: Calculated: 403.1; Observed: 403.8 (M++1).

Workup

  1. temperatureupon completion the reaction mixture was cooled to 0° C.
  2. customwas quenched with ice
  3. customThe reaction mixture was partitioned between DCM
  4. extractionextracted with DCM
  5. customThe combined organics were purified by silica gel chromatography, EA/hexanes gradient

Sources & evidence

ORD record
ord-8c782390e4c5493b9f788e3d04be969f
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

Loading…