HCID 68194963, compound → HCID 136209611, compound

HRID 2169615Notes

Reaction equation

HRID 2169615 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][CH:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1.CC1(C)C(C)(C)OB([C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH:26]=[C:27]([OH:33])[NH:28]3)O1>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]>[N:3]1[C:4]2[N:5]3[CH2:15][CH2:14][O:13][CH2:12][CH:6]3[CH2:7][NH:8][C:9]=2[CH:10]=[N:11][C:2]=1[C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH:26]=[C:27]([OH:33])[NH:28]2

Participants

6

Reactant 2

HCID 68194963HCID 68194963, compoundHCID 86670087HCID 86670087, compound

Product 1

HCID 136209611HCID 136209611, 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 1 using 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 50 mg, 0.221 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-2-ol (30 mg, 0.116 mmol), and PdCl2(dppf) (12.91 mg, 0.018 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.95-3.03 (m, 2 H), 3.20-3.30 (m, 3 H), 3.77-3.83 (m, 2 H), 3.88-3.95 (m, 1 H), 4.00-4.08 (m, 1 H), 4.36-4.45 (m, 1 H), 6.01-6.15 (m, 1 H), 6.78-6.85 (m, 1 H), 7.18-7.26 (m, 1 H), 7.62-7.68 (m, 1 H), 7.74-7.80 (m, 1 H), 10.23-10.52 (m, 1 H), 12.27-12.56 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C17H17N5O2, 323.14; found 324.3.

Sources & evidence

ORD record
ord-d7ef6d18ce3b43e096e6a4a413ec65ca
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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