Methyl iodide → HCID 71209368, compound

HRID 1912626Notes

Reaction equation

HRID 1912626 reaction equation
[CH3:1][C:2]1[C:11]2[NH:10][CH2:9][CH2:8][O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[B:12]1[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]1.I[CH3:22]>CN(C)C=O.C(OCC)(=O)C>[CH3:22][N:10]1[CH2:9][CH2:8][O:7][C:6]2[CH:5]=[CH:4][C:3]([B:12]3[O:13][C:14]([CH3:20])([CH3:19])[C:15]([CH3:18])([CH3:17])[O:16]3)=[C:2]([CH3:1])[C:11]1=2

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 59578516HCID 59578516, compound

Product 1

HCID 71209368HCID 71209368, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

An ice cold mixture of 5-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (65.0 mg, 0.236 mmol) in N,N-dimethylformamide (DMF) (0.5 mL) was treated with iodomethane (0.044 mL, 0.709 mmol) and the mixture was stirred at ambient temperature overnight. The mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate, water, brine, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (hexanes/ethyl acetate) to afford a pale yellow residue (40 mg, 59%): 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.39 (d, J=8.2 Hz, 1 H), 6.69 (d, J=8.2 Hz, 1 H), 4.20-4.14 (m, 2 H), 3.12-3.03 (m, 2 H), 2.66 (s, 3 H), 2.49 (s, 3 H), 1.31 (s, 12 H); LC/MS (m/z) ES+=290 (M+1).

Workup

  1. washwashed with saturated sodium bicarbonate, water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9d19ec58eb934aac8c112cce4715fc06
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

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