Triethylamine → HCID 66649728, compound

HRID 420292Notes

Reaction equation

HRID 420292 reaction equation
[NH2:1][C:2]1[C:31](I)=[CH:30][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:4][C:3]=1[F:33].[CH3:34][CH2:35]N(CC)CC.C([B-](F)(F)F)=C.[K+]>C(O)CC.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Ar].Cl[Pd]Cl>[NH2:1][C:2]1[C:31]([CH:34]=[CH2:35])=[CH:30][C:5]([CH2:6][C@H:7]2[C@H:15]3[C@@H:11]([N:12]([CH2:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH:19]=4)[C:13](=[O:16])[O:14]3)[CH2:10][S:9](=[O:29])(=[O:28])[CH2:8]2)=[CH:4][C:3]=1[F:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 57386048HCID 57386048, compound

Product 1

HCID 66649728HCID 66649728, compound

Reagents, catalysts & solvents 2

HCID 178419112HCID 178419112, compoundCatalystHCID 10311-PropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (3aR,7S,7aS)-7-(4-amino-3-fluoro-5-iodo-benzyl)-3-(3-tert-butyl-benzyl)-5,5-dioxo-hexahydro-1-oxa-5lambda*6*-thia-3-aza-inden-2-one (0.65 g, 1.1 mmol), NEt3 (0.54 mL, 3.9 mmol) and potassium vinyltrifluoroborate (0.39 g, 2.7 mmol) in n-propanol (20 mL) was added after degassing with argon (1,1′-bis(diphenylphosphino)ferrocene)-dichloro-palladium (0.063 g, 0.078 mmol) and the reaction mixture was heated at 90° C. for 3.5 h. After dilution with saturated NaHCO3 solution the product was extracted with EtOAc. Combined organic extracts were washed with brine, dried over MgSO4, filtered and evaporated. The title compound was obtained after chromatographic purification (Combi Flash, 40 g, hexane-EtOAc 5:95 to 0:100) as a yellow solid: TLC (toluene-EtOAc 3:1) Rf=0.38; UPLC RtD=1.756 min; ESIMS [M+NH4]+=504; 1H NMR (400 MHz, CDCl3): δ 7.38 (d, 1H), 7.30 (m, 2H). 7.09 (d, 1H), 6.80 (s, 1H), 6.72 (dd, 1H), 6.66 (d, 1H), 5.64 (d, 1H), 5.39 (d, 1H), 4.53 (d, 1H), 4.33 (d, 1H), 3.7-3.9 (m, 4H), 3.05 (m, 3H), 2.82 (dd, 1H), 2.72 (m, 1H), 2.60 (m, 2H), 1.31 (s, 9H).

Workup

  1. extractionAfter dilution with saturated NaHCO3 solution the product was extracted with EtOAc
  2. washCombined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-616f9616ee744f10bd2d59c623e187e5
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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