Triethyl phosphite → HCID 59172007, compound

HRID 1952422Notes

Reaction equation

C([O:3][P:4]([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])C.Br[CH2:12][CH2:13][CH2:14][N:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2>>[CH:17]1[C:16]2[N:15]([CH2:14][CH2:13][CH2:12][P:4](=[O:3])([O:5][CH2:6][CH3:7])[O:8][CH2:9][CH3:10])[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

Reactant 2

HCID 31215Triethyl phosphite

HCID 10732069N-(3-Bromopropyl)carbazole

Product 1

HCID 59172007HCID 59172007, compoundYield 92.2%

Conditions

Temperature: 130 °C

Procedure

Triethylphosphite (13.4 mL, 80.1 mmol) was added via syringe to 9-(3-bromopropyl)-9H-carbazole (7.70 g, 26.7 mmol) in a 50 mL rbf. The reaction was heated and stirred under Argon at 130° C. for 18 hours. Excess triethylphosphite and side-products were removed under vacuum at ˜100° C. to yield a thick yellow oil (8.50 g, 92% yield). 1H NMR (400.14 MHz, CD2Cl2) δ 8.10 (dt, J=7.73, 2.00 Hz, 2H), 7.50-7.44 (m, 4H), 7.27-7.19, m, 2H), 4.43 (t, J=7.00 Hz, 2H), 4.10-3.95 (m, 4H), 2.23-2.09 (m, 2H), 1.74 (dt, J=18.41, 7.80 Hz, 2H), 1.26 (t, J=7.00 Hz, 6H). 13C{1H} NMR (100.62 MHz, CD2Cl2) δ 139.99 (2C), 125.36 (2C), 122.42 (2C), 119.88 (2C), 118.56 (2C), 108.37 (2C), 61.18 (d, J=6.44 Hz), 42.52 (d, J=15.39 Hz), 22.59 (d, J=141.97 Hz), 21.75 (J=4.83 Hz), 15.91 (d, J=5.84 Hz). 31P{1H} NMR (161.97 MHz, CD2Cl2): δ 31.22. Analysis found (calculated) %: C, 65.67 (66.07); H, 7.01 (7.00); N, 4.05 (4.06). MS (EI, m/z): 290 ([M], 100%). Exact mass found (calculated for [M], m/z): 345.14264 (345.14938).

Workup

temperatureThe reaction was heated
customExcess triethylphosphite and side-products were removed under vacuum at ˜100° C.

Sources & evidence

ORD record: ord-5a9c5faa391849758b952d7c57d15430
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08405069B2

Reaction notes

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