Water → 5-Bromo-7-(4-bromobutyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1972781Notes

Reaction equation

[NH2:1][C:2]1[C:7]2=[C:8]([Br:16])[CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][CH2:14]O)[N:6]2[N:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:37].O>O1CCCC1>[Br:16][C:8]1[CH:9]=[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][Br:37])[N:6]2[C:7]=1[C:2]([NH2:1])=[N:3][CH:4]=[N:5]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of 4-(4-amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)butan-1-ol (600 mg, 2.10 mmol) and triphenylphosphine (828 mg, 3.16 mmol) in tetrahydrofuran (15 mL) was added carbon tetrabromide (837 mg, 2.53 mmol). The reaction was stirred (0° C.) for 90 min and then was warmed to rt and stirred an additional 1 h. Water (25 mL) was added and the mixture was extracted with ethyl acetate (2×25 mL). The combined organics were dried (Na2SO4) and evaporated. The crude material was purified via ISCO® chromatography using a gradient of 25 to 50% ethyl acetate in hexanes to afford 597 mg (82%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.82 (s, 1 H), 6.62 (s, 1 H), 3.54 (t, 2 H), 2.84 (t, 2 H), 1.86-1.70 (m, 4 H); ES-MS m/z 347.2 [M+H]+, HPLC RT (min) 2.58.

Workup

temperaturewas warmed to rt
stirringstirred an additional 1 h
extractionthe mixture was extracted with ethyl acetate (2×25 mL)
dry with materialThe combined organics were dried (Na2SO4)
customevaporated
customThe crude material was purified via ISCO® chromatography

Sources & evidence

ORD record: ord-eb0514e06f544507a185e876d2894db8
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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