Cesium carbonate → HCID 86696904, compound

HRID 1399994Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([C:22]3[CH:23]=[N:24][C:25](C(O)(C)C)=[N:26][CH:27]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].BrC1C=NC([CH2:39][P:40]([O:45][CH2:46][CH3:47])([O:42][CH2:43][CH3:44])=[O:41])=NC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:43]([O:42][P:40]([CH2:39][C:25]1[N:24]=[CH:23][C:22]([C:13]2[CH:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:9]3[S:8][C:7]([NH:6][C:4]([NH:3][CH2:1][CH3:2])=[O:5])=[N:11][C:10]=3[CH:12]=2)=[CH:27][N:26]=1)([O:45][CH2:46][CH3:47])=[O:41])[CH3:44]

Participants

Conditions

Temperature: 100 °C

Procedure

Intermediate 1 (860 mg, 2.5 mmol), iii (813 mg, 2.63 mmol), Cs2CO3 (2.57 g, 7.90 mmol) and Pd(PPh3)2Cl2 (90 mg, 0.10 mmol) were dissolved in 1-4-dioxane:H2O (10:1; 10 mL) and degassed with a stream of N2 for 10 min. The reaction was sealed under an atmosphere of N2 and heated at 100° C. for 1 h in a microwave reactor. The mixture was concentrated in vacuo, purified over silica (gradient elution: 0-10% DCM-MeOH) and triturated from acetone affording iv (410 mg, 29%). MS: 527.1 [M+H]+.

Workup

customdegassed with a stream of N2 for 10 min
customThe reaction was sealed under an atmosphere of N2
concentrationThe mixture was concentrated in vacuo
custompurified over silica (gradient elution: 0-10% DCM-MeOH)
customtriturated from acetone affording iv (410 mg, 29%)

Sources & evidence

ORD record: ord-c1a13da53f78486da2f6b79c40af1477
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906902B2

Reaction notes

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