Triethylamine → 4-(2,3-Dihydroindol-1-yl)-6-iodoquinazoline

HRID 1469085Notes

Reaction equation

HRID 1469085 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.C(N(CC)CC)C.N1C2C(=CC=CC=2)C=NC=1>O1CCOCC1>[N:13]1([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([I:12])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9210QuinazolineHCID 10328IndolineHCID 111738094-Chloro-6-iodoquinazoline

Product 1

HCID 675130954-(2,3-Dihydroindol-1-yl)-6-iodoquinazolineYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.60 g of 4-chloro-6-iodoquinazoline, 0.31 ml of 2,3-dihydro-1H-indole and 0.50 ml of triethylamine in 5.00 ml of dioxane are heated at 80° C. in a flask until the quinazoline has reacted completely (HPLC check, about 24 hours). The cooled reaction solution is evaporated to dryness in a rotary evaporator. The residue is purified by means of column chromatography (gradient EA: methanol 0-20% in 16 min.), giving 0.60 g of 4-(2,3-dihydroindol-1-yl)-6-iodoquinazoline as yellowish solid (yield 85%, content 97%); MS-FAB (M+H+)=373.8; Rf (polar method): 2.21 min.

Workup

  1. customhas reacted completely (HPLC check, about 24 hours)
  2. customThe cooled reaction solution
  3. customis evaporated to dryness in a rotary evaporator
  4. customThe residue is purified by means of column chromatography (gradient EA: methanol 0-20% in 16 min.)

Sources & evidence

ORD record
ord-9cf23791a2474af1889954c53c7bc594
Source dataset
uspto-grants-2015_04
Patent number
US09006255B2

Reaction notes

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