Methanol → HCID 68864807, compound

HRID 1725929Notes

Reaction equation

HRID 1725929 reaction equation
Br[C:2]1[C:3]([Cl:29])=[C:4]([C:15]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:16][CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[F-].[Cs+].CO[CH2:34][CH2:35]OC.CO>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:29][C:3]1[C:2]([CH:34]=[CH2:35])=[CH:17][CH:16]=[C:15]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:4]=1[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

7

Reactant 4

HCID 887MethanolHCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 68865572HCID 68865572, compound

Product 1

HCID 68864807HCID 68864807, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 226E (160 mg, 0.32 mmol), dibutyl vinylborate (88 mg, 0.48 mmol), CsF (146 mg, 0.96 mmol), Pd(PPh3)4 (37 mg, 0.03 mmol), DME (3.2 mL) and methanol (1.6 mL) was purged with argon, sealed in a vial and microwaved at 150° C. for 240 seconds. The mixture was diluted with ethyl acetate (50 mL), washed with brine, dried (Na2SO4), filtered, concentrated and purified on a Biotage silica gel cartridge (40 g) with 10% ethyl acetate/hexanes to provide the desired product. MS (ESI(+)) m/e 446 (M+H)+, 463 (M+NH)+, 468 (M+Na)+; (ESI(−)) m/e 444 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.36 (s, 1H), 7.76 (m, 3H), 7.38 (m, 7H), 7.10 (d, 1H), 6.93 (dd, 1H), 5.86 (d, 1H), 5.51 (d, 1H), 5.26 (s, 2H).

Workup

  1. customsealed in a vial and
  2. custommicrowaved at 150° C. for 240 seconds
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on a Biotage silica gel cartridge (40 g) with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8ad3bc017400463d9d0effe504fa564a
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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