Tetrahydrofuran → HCID 70981496, compound

HRID 1475448Notes

Reaction equation

HRID 1475448 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([CH:17]=[O:18])[N:13]=[CH:12][C:11]=2[C:10]([CH3:20])([CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]1[CH2:25]OC[CH2:22]1>>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[C:14]([CH:17]([OH:18])[CH:21]([CH3:25])[CH3:22])[N:13]=[CH:12][C:11]=2[C:10]([CH3:20])([CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 86724023HCID 86724023, compound

Product 1

HCID 70981496HCID 70981496, compound

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 6-formyl-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.65 g, 2.36 mmol), in THF (20 mL) at −78° C. under nitrogen was added, dropwise over 0.1 h, a solution of isopropylmagnesium chloride-lithium chloride complex in THF (1.3 M, 2.7 mL, 3.53 mmol). Resulting solution was stirred at −78° C. then was quenched with aqueous citric acid (5%, 30 mL) and extracted with DCM (4×50 mL). Combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give a foam. Chromatography (SiO2; gradient elution with 0-100% EtOAc in 40-60 petroleum ether) gave the title compound (0.398 g). 1H NMR (Me-d3-OD): 8.15 (1H, s), 8.08-7.45 (1H, m), 4.41 (1H, d), 3.78 (2H, s), 2.10-1.97 (1H, m), 1.60 (9H, s), 1.40 (6H, d), 0.92 (6H, t).

Workup

  1. customthen was quenched with aqueous citric acid (5%, 30 mL)
  2. extractionextracted with DCM (4×50 mL)
  3. dry with materialCombined organic extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customto give a foam
  6. washChromatography (SiO2; gradient elution with 0-100% EtOAc in 40-60 petroleum ether)

Sources & evidence

ORD record
ord-119875c2b6a645dcb74259e9580dc7b7
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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