Cesium carbonate → HCID 86706699, compound

HRID 1468087Notes

Reaction equation

HRID 1468087 reaction equation
Br[C:2]1[CH:37]=[C:36]2[C:5]([CH2:6][C:7]3([C:15]42[N:19]=[C:18]([N:20]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17]([CH3:35])=[N:16]4)[CH2:12][CH2:11][CH:10]([O:13][CH3:14])[CH2:9][CH2:8]3)=[CH:4][C:3]=1[F:38].C(P(C(C)(C)C)C1C(OC)=CC=C(C)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+].[F:78][CH2:79][CH2:80][CH2:81][OH:82]>[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]>[F:38][C:3]1[CH:4]=[C:5]2[C:36](=[CH:37][C:2]=1[O:82][CH2:81][CH2:80][CH2:79][F:78])[C:15]1([N:19]=[C:18]([N:20]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17]([CH3:35])=[N:16]1)[C:7]1([CH2:12][CH2:11][CH:10]([O:13][CH3:14])[CH2:9][CH2:8]1)[CH2:6]2

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 680423-Fluoro-1-propanol2×HCID 56641709(2',4'-Diisopropyl-3-methoxy-6-methyl-6'-propyl-2-biphenylyl)[bis(2-methyl-2-propanyl)]phosphineHCID 86706700HCID 86706700, compound2×

Product 1

HCID 86706699HCID 86706699, compound

Reagents, catalysts & solvents 1

HCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-Catalyst

Conditions

Temperature
90 °C

Procedure

Di-tert-butyl (6′-bromo-5′-fluoro-4-methoxy-5″-methyl-3′H-dispiro[cyclohexane-1,2′-indene-1′,2″-imidazol]-4″-yl)imidodicarbonate (Intermediate 15, 0.261 g, 0.44 mmol), di-tert-butyl(2′,4′,6′-triisopropyl-3-methoxy-6-methylbiphenyl-2-yl)phosphine (0.012 g, 0.03 mmol), cesium carbonate (0.053 mL, 0.66 mmol), allylpalladium chloride dimer (3.1 mg, 8.78 μmol) and 3-fluoropropan-1-ol (0.069 g, 0.88 mmol) were placed in a tube. The tube was capped and inerted by vacuum-nitrogen purge cycles. Toluene (3 mL) was added and the mixture was heated at 90° C. o.n. More 3-fluoropropan-1-ol (0.069 g, 0.88 mmol) was added, and the reaction was heated for another 3 h. The mixture was allowed to cool to r.t. and was then filtered and concentrated. The product was used directly in the next step.

Workup

  1. customThe tube was capped
  2. custompurge cycles
  3. additionToluene (3 mL) was added
  4. temperaturethe reaction was heated for another 3 h
  5. temperatureto cool to r.t.
  6. filtrationwas then filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e5ad7677dac0406c90aa1da3bc093bc4
Source dataset
uspto-grants-2015_04
Patent number
US09000183B2

Reaction notes

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