Potassium Carbonate → HCID 18932892, compound

HRID 1597967Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:22])=[C:18]([OH:21])[CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].O.O.O.O.O.[OH-].C[N+](C)(C)C.[CH2:40]([CH:42]1[O:44][CH2:43]1)Br>CN(C=O)C.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[C:11]2[C:20]3[C:15](=[CH:16][C:17]4[O:22][CH2:40][CH:42]([CH2:43][OH:44])[O:21][C:18]=4[CH:19]=3)[N:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To 4-(6-chloro-2,3-dihydro-indol-1-yl)-quinazoline-6,7-diol (99 mg, 0.316 mmol; from Example 69) dissolved in DMF (2 mL) was added H2O (100 μL), K2CO3 (s) (65 mg, 0.473 mmol), and tetramethylammonium hydroxide pentahydrate (11 mg, 0.06 mmol) followed by epibromohydrin (28 μL, 0.331 mmol). The mixture was stirred at 50° C. under N2(g) for 16 hours. Following extractive work-up, and chromatography on silica (20% acetone/CH2Cl2) analogous to that described for Example 78 the product was obtained in 11% yield. (M.P. 219°-222° C. (dec); LC-MS: 370 (MH+); anal. RP18-HPLC RT: 3.98 min.).

Workup

customwas obtained in 11% yield

Sources & evidence

ORD record: ord-ed260943d9d14fa584b965e7587255f9
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05736534

Reaction notes

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