Cesium carbonate → HCID 57590935, compound

HRID 1783767Notes

Reaction equation

[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8]/[CH:9]=[CH:10]/B1OC(C)(C)C(C)(C)O1)([CH3:4])([CH3:3])[CH3:2].Br[C:22]1[C:31]2[C:26](=[CH:27][C:28]3[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=3[CH:30]=2)[C:25]2=[N:36][NH:37][C:38](=[O:39])[N:24]2[CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8]/[CH:9]=[CH:10]/[C:22]1[C:31]2[C:26](=[CH:27][C:28]3[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=3[CH:30]=2)[C:25]2=[N:36][NH:37][C:38](=[O:39])[N:24]2[CH:23]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of tert-butyl[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]carbamate (3-3) (32.5 mg, 0.115 mmol, 4 eq) and 6-bromobenzo[g][1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (7-6) (9.0 mg, 0.029 mmol, 1 eq) in THF (0.5 ml) was added a solution of cesium carbonate (18.7 mg, 0.058 mmol, 2 eq) in water (0.2 ml), and the resulting mixture was deoxygenated with nitrogen and treated with Pd(dppf) (1.0 mg, 0.0014 mmol, 0.05 eq). The reaction mixture was deoxygenated again, and heated in a sealed tube under microwave irradiation for 8 min at 150° C. The resulting suspension was filtered through a pad of Celite washing with DMF, and the filtrate was purified on RP HPLC (MeCN/Water with TFA) to afford the desired coupling product 7-7. LRMS m/z: found 391.2, calcd. (M+H) 391.2.

Workup

customthe resulting mixture was deoxygenated with nitrogen
customThe reaction mixture was deoxygenated again
filtrationThe resulting suspension was filtered through a pad of Celite
washwashing with DMF
customthe filtrate was purified on RP HPLC (MeCN/Water with TFA)

Sources & evidence

ORD record: ord-fbe5aaabac674098a7b0bd0b478e03f5
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501435B2

Reaction notes

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