Trimethyl borate → HCID 58557261, compound

HRID 1969663Notes

Reaction equation

[CH:1]1([C:7]2[N:11]3[C:12]4[C:18](I)=[CH:17][N:16]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:13]=4[N:14]=[CH:15][C:10]3=[N:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:28](=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.COB(OC)OC>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:1]1([C:7]2[N:11]3[C:12]4[C:18]([CH3:28])=[CH:17][N:16]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[C:13]=4[N:14]=[CH:15][C:10]3=[N:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 85 °C

Procedure

To the solution of 8-cyclohexyl-1-iodo-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.100 g, 0.201 mmol, prepared using GGG with 8-cyclohexyl-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine [WO2009152133A1], KK) in 1,4-dioxane (1 mL) was added cesium carbonate (0.131 g, 0.403 mmol), tricyclohexylphosphine (20 wt % solution in toluene, 0.045 g, 0.032 mmol), Pd2(dba)3 (0.018 g, 0.020 mmol) and trimethylborate (0.033 g, 0.262 mmol). The mixture was degassed and heated at about 85° C. for about 2 h. The catalyst was filtered off. The filtrate was concentrated and purified by RP-HPLC (Table 1, Method s) to give 8-cyclohexyl-1-methyl-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.032 g, 41%) as a clear oil: LC/MS (Table 1, Method b) Rt=3.41 min; MS m/z: 385 (M+H)+.

Workup

customThe mixture was degassed
filtrationThe catalyst was filtered off
concentrationThe filtrate was concentrated
custompurified by RP-HPLC (Table 1, Method s)

Sources & evidence

ORD record: ord-18552eef81e34ff7a3cb685e24ac0d97
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426411B2

Reaction notes

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