Potassium Carbonate → HCID 68085822, compound

HRID 514066Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17](B3OC(C)(C)C(C)(C)O3)[CH:18]=2)[C:13]=1[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].Br[C:40]1[N:45]=[CH:44][CH:43]=[CH:42][N:41]=1.C([O-])([O-])=O.[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1.CCO>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:40]3[N:45]=[CH:44][CH:43]=[CH:42][N:41]=3)[CH:18]=2)[C:13]=1[C:32]1[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-Ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)acetate (0.072 g, 0.13 mmol), 2-bromopyrimidine (0.032 g, 0.20 mmol), PdCl2(dppf) (0.005 g, 0.007 mmol) were taken up in 3/1 PhMe/EtOH (1 mL). The resulting solution was treated with 2 M K2CO3 (0.35 mL, 0.70 mmol), sealed and sparged with Ar for 10 min. After 2.5 h of heating at 50° C. and cooling to room temperature, the crude reaction mixture was purified by Yamazen column chromatography (20-100% EtOAc/Hex) to produce 0.042 g (64%) of a colorless film. LCMS-ESI+ (m/z): [M]+ calcd for C29H29ClN2O3: 489.01; found: 489.51.

Workup

customsealed
customsparged with Ar for 10 min
temperaturecooling to room temperature
customthe crude reaction mixture
customwas purified by Yamazen column chromatography (20-100% EtOAc/Hex)
customto produce 0.042 g (64%) of a colorless film

Sources & evidence

ORD record: ord-26be46ac40c74b4ab8eb447cab33930a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102614B2

Reaction notes

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