1H-Indole-4-boronic acid → HCID 68197777, compound

HRID 1631760Notes

Reaction equation

HRID 1631760 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][CH2:13][CH:14]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:7][C@@H:6]3[CH2:27][O:28][CH2:29][CH2:30][N:5]3[C:4]=2[N:3]=1.[NH:31]1[C:39]2[C:34](=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32]1>O1CCOCC1.C([O-])(O)=O.[Na+].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]>[NH:31]1[C:39]2[C:34](=[C:35]([C:2]3[N:11]=[CH:10][C:9]4[N:8]([CH2:12][CH2:13][CH:14]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:7][C@@H:6]5[CH2:27][O:28][CH2:29][CH2:30][N:5]5[C:4]=4[N:3]=3)[CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32]1

Participants

6

Reactant 2

HCID 27631731H-Indole-4-boronic acidHCID 86670143HCID 86670143, compound

Product 1

HCID 68197777HCID 68197777, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The title compound was prepared in a manner similar to Example 2 using tert-butyl (1-((R)-2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)-4,4-dimethylpentan-3-yl)carbamate (PREPARATION x77, 53 mg, 0.120 mmol), 1H-indol-4-ylboronic acid (38.8 mg, 0.241 mmol) and PdCl2(dppf) (4.41 mg, 0.006 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL) (19 mg, 30%). ESI-MS m/z [M+H]+ calc'd for C29H40N6O3, 521.32. found 521.5.

Sources & evidence

ORD record
ord-3de1e7105d1447bb92bd8bbf2dff9ab3
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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