Methyl iodide → tert-butyl N-(2-chloro-3-methylfuro[2,3-c]pyridin-7-yl)-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate

HRID 389425Notes

Reaction equation

HRID 389425 reaction equation
[Cl:1][C:2]1[O:25][C:5]2=[C:6]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.[Li+].[CH3:27]C([N-]C(C)C)C.CI>C1COCC1>[Cl:1][C:2]1[O:25][C:5]2=[C:6]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 66760259HCID 66760259, compound

Product 1

HCID 66760298tert-butyl N-(2-chloro-3-methylfuro[2,3-c]pyridin-7-yl)-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamateYield 102.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Di-tert-butyl (2-chlorofuro[2,3-c]pyridin-7-yl)imidodicarbonate (3.0 g, 8.15 mmol) in dry THF (100 mL) was cooled to −65° C. to −75° C. and LDA (1.8 M in THF/heptanes/ethylbenzene, 6.0 mL, 10.8 mmol), pre-cooled to the same temperature, was added slowly via syringe over a period of 10 min. The mixture was stirred for 1.5 h at −65° C. to −75° C. and then treated with methyl iodide (0.76 mL, 12.2 mmol) in dry THF added slowly via syringe. The mixture was allowed to warm to RT overnight and was quenched by the addition of water (50 mL) and diluted with EtOAc (100 mL). The phases were separated and the organic phase was dried over Na2SO4, and concentrated in vacuo leaving 3.2 g of a brown solid which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 8.25 (d, J=5.5 Hz, 1H), 7.39 (d, J=5.5 Hz, 1H), 2.22 (s, 3H), 1.40 (s, 18H).

Workup

  1. additionwas added slowly via syringe over a period of 10 min
  2. additionadded slowly via syringe
  3. customwas quenched by the addition of water (50 mL)
  4. additiondiluted with EtOAc (100 mL)
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ae425002bf5418b8fbf69cb235c7c18
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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