Methanesulfonic Acid → HCID 59290439, compound

HRID 909927Notes

Reaction equation

HRID 909927 reaction equation
CS(O)(=O)=O.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]=[CH:14][O:15]C)[C:8]=1[F:17].C(=O)(O)[O-].[Na+].[BH4-].[Na+]>O.O1CCCC1>[Br:6][C:7]1[C:8]([F:17])=[C:9]([CH2:13][CH2:14][OH:15])[CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 6395Methanesulfonic AcidHCID 516892Sodium Bicarbonate2×HCID 4311764Sodium borohydrideHCID 67076147HCID 67076147, compound

Product 1

HCID 59290439HCID 59290439, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Methanesulfonic acid (0.4 mL) was added to a mixture of 1-bromo-2-fluoro-3-(2-methoxyvinyl)benzene [Example 16, Step i)] (1.8 g), tetrahydrofuran (15 mL) and water (1.5 mL) and sealed into a microwave tube. The reaction was heated to 80° C., over a period of 90 min in the microwave reactor. Sodium bicarbonate (654 mg) was added portionwise and the mixture was stirred for 10 min. Sodium borohydride (295 mg) was added portionwise (gas evolution) and the mixture was stirred for 30 min. The reaction mixture was poured into saturated sodium hydrogen carbonate solution and extracted with DCM (3×30 mL). The organic was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 30% ethyl acetate in isohexane to afford the subtitled compound (1.26 g) as a liquid. 1H NMR (300 MHz, CDCl3) δ 7.47-7.40 (m, 1H), 7.23-7.16 (m, 1H), 6.97 (t, J=7.8 Hz, 1H), 3.88 (q, J=6.2 Hz, 2H), 2.95 (t, J=6.5 Hz, 2H), 1.43 (t, J=5.7 Hz, 1H).

Workup

  1. customsealed into a microwave tube
  2. stirringthe mixture was stirred for 30 min
  3. extractionextracted with DCM (3×30 mL)
  4. dry with materialThe organic was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product
  8. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 30% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-7ea2f05b8ad648debe895085d510433a
Source dataset
uspto-grants-2011_09
Patent number
US08017602B2

Reaction notes

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